Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 1976-1982.DOI: 10.6023/cjoc201812020 Previous Articles     Next Articles



李蔚a, 宿亮a, 汪秋安a, 李高阳b, 单杨b   

  1. a 湖南大学化学化工学院 长沙 410082;
    b 湖南省农业科学院农产品加工研究所 长沙 410125
  • 收稿日期:2018-12-11 修回日期:2019-03-01 发布日期:2019-03-29
  • 通讯作者: 汪秋安
  • 基金资助:


Synthesis of 8-Prenylflavonoids Natural Products by Microwave Promoted Claisen Rearrangement

Li Weia, Shu Lianga, Wang Qiuana, Li Gaoyangb, Shan Yangb   

  1. a College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082;
    b Institution of Agricultural Product Processing, Hunan Academy of Agricultural Science, Changsha 410125
  • Received:2018-12-11 Revised:2019-03-01 Published:2019-03-29
  • Contact: 10.6023/cjoc201812020
  • Supported by:

    Project supported by the Key Laboratory of Hunan Province for Fruit and Vegetable Processing and Quality Safety (No. 2108TP1030) and the Hunan Provincial Natural Science Foundation of China (No. 2018JJ2034).

8-Prenylflavonoids are a class natural products with significant biological activities. The total synthesis of three prenylflavonoid natural products, 8-prenylquercetin-3-methylether (1), 8-prenylquerccetin-3,7,3',4'-tetramethyl ether (2) and Artochamin C (3), was achieved through methoxymethyl protection, aldol condensation, iodine catalytic cyclization, dimethyl sulfoxide (DMSO) oxidation, O-prenylation, microwave promoted Claisen rearrangement, deprotection, O-methylation and prenyl group side chain cyclization, staring from commercially available 2,4,6-trihydroxyacetophenone and 3,4-dihydroxy benzaldehyde. The key step of microwave promoted Claisen rearrangement formed 8-C-prenylflavonoids from 5-O- prenylflavonoids was investigated. All the synthesized compounds were confirmed by 1H NMR、13C NMR and MS techniques.

Key words: 8-prenylquercetin-3-methyl ether, 8-prenylquercetin-3,7,3',4'-tetramethyl ether, artochamin C, microwave promoted Claisen rearrangement